YAKUGAKU ZASSHI
Online ISSN : 1347-5231
Print ISSN : 0031-6903
ISSN-L : 0031-6903
3H-Indoleの研究(第3報)Acyl Chloride付加体の転位反応 その2
高山 和男原野 一誠田口 胤三
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1974 年 94 巻 5 号 p. 548-552

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In connection with studies on pyrolysis of 3, 3-disubstituted 1-acyl-indolin-2-ylpyridinium chloride, 1) 2, 3, 3-trisubstituted 1-acyl-indolin-2-ylpyridinium chlorides (Ia-c) were analogously pyrolyzed in boiling pyridine. Of the compounds treated, only derivatives holding a methyl substituent at position 2 (Ib, c) underwent pyrolysis giving 3, 3-disubstituted 1-(p-chlorobenzoyl)-2-methylene-indoline (IIb, c). During the isolation of IIb and IIc, 1-(p-chlorobenzoyl)-2, 3-dimethyl-3-phenylindolin-2-ol (IVb) and 3-[2-(p-chlorobenzoyl-anilino)]-3-methyl-2-butanone (IIIc) were respectively found in the reaction mixture. The tautomeric character of these compounds (IVb and IIIc) existing in the indolin-2-ol and its ring opening structures in solution was discussed. Additionally, this report involves a correction of the product in the Friedel-Crafts reaction of 1-benzoyl-2-chloro-3, 3-dimethyl-indoline with benzene reported by Leuchs.3)

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